


Initiation game

by peachypeppers



Category: Check Please! (Webcomic)
Genre: Dom Jack, Happy Halloween you kinky fucks, M/M, Other, Roleplay, Sexual Roleplay, Spanking, Sub Bitty, Trans Eric "Bitty" Bittle, Vaginal Fingering, established D/s relationship, hole spanking, paddles
Language: English
Status: Completed
Published: 2019-10-02
Updated: 2019-10-02
Packaged: 2020-10-24 19:02:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 796
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20710976
Author URL: https://archiveofourown.org/users/peachypeppers/pseuds/peachypeppers
Summary: **originally part of kinktober,  now stand alone*If Bitty wants to be on Samwells hockey team, hes gotta prove himself





	Initiation game

Not every whispered fantasy between Jack and Bitty is one they plan to fulfill. Some just aren't feasible, while others they're only interested in theoretically. 

This one, though, has Jack making a contemplative face when Bitty shares it.

"We...we should try that sometime."

They talk about it again in the morning, and Bitty briefly muses how much chirping they'd get if their friends knew how often breakfast conversation between him and Jack turns to kink negotiation

—— 

Bittys heart is thumping in his chest, blindfolded and with his arms behind his back, kneeling on the cold floor, in nothing but a pair of tiny sleep shorts. He has no idea what Jack is saying, too nervous to really follow his captains words. Something about brotherhood and hockey? Currently, the  _ tap, tap, tap _ of what Bitty knows is a wooden paddle smacking against Jacks palm is all too distracting, as is the stirring of arousal between Bittys legs.

“ _ Bittle _ .” Jack snaps suddenly, making the smaller jump in surprise “Get in position. For your initiation, you'll take ten strikes with the paddle without complaint."

Slowly, Bitty does as he’s told, pulling his shorts down just below his ass cheek, and leans forward on his hands and knees.

Jacks makes a contemplative noise, then reaches down to cup Bittys ass in his hand and squeeze while Bitty squirms under the attention, face hot.

"Bet you won't even feel it, your ass is so thick."

The paddle collides with Bittys ass suddenly, clearly testing the waters, but it draws a quiet ‘ _ oh _ ’ from Bitty regardless. The second one is harder, more sure, making Bitty bite his tongue around a yelp, but he keeps still, desperately trying to ignore the arousal and wetness growing between his legs. There’s barely a chance to catch his breath before a third and fourth strike hit him rapidly, a filthy moan falling from Bittys lips, most definitely not one of pain.

Jack pauses, and the only sound in the room is Bittys heavy panting. Then, Jack’s hand trails across Bittys ass, gentle and cool against Bittys red and stinging cheeks. They make little swirls across Bittys skin, but as suddenly as they’re felt, they're replaced by the fifth strike, forcing a startled “oh  _ shit _ -" out of him.

"That's gonna be three more strikes, Bittle." Jack snaps, adding a sixth hit across Bittys sore bottom. This time, Jacks wandering fingers slide down Bittys ass and over his dripping hole, drawing a squeak out of him.

"You enjoying this?" Jack murmurs, watching as Bitty arches his back and moans while Jack quickly screws a finger in and out of Bittys hole. 

The seventh, eighth, and ninth strike across Bittys ass come with Jacks finger still thrusting inside of Bitty, not enough sensation to make him come, but enough to drive Bitty crazy as he skirts the line between stinging pain from the paddle and Jack toying with his hole.

"Just four more, Bittle.

Jack finally pulls his finger back out, and Bitty braces himself for the tenth strike, but instead Jack puts the paddle down. Bitty turns towards the sound, but Jacks hand is on his back, keeping him still. The other hand smacks hard between Bittys legs, over his hole, making him yelp. The hand still firmly on Bittyd back keeps him from squirming away from Jacks hand.

"Don't start misbehaving now." Jack says sharply, rubbing between Bittys folds "Or do you want more, seeing how much you enjoy it."

"I'll be good, I promise." Bitty says, voice breathy.

"Then hold still." Jack delivers the last three spanks over Bittys hole, drawing sharp cries with every hit, but true to his word, Bitty doesn't move away from them.

"You did so good." Jack murmurs, stroking his hand over Bittys ass gently "Took your initiation well. I think you earned a reward."

Bitty gasps softly as two of Jacks fingers work their way into his sensitive hole, while Jacks thumb starts to work over his dick in circles. Jack watches as Bitty pants and whines and moans on his fingers, fucking himself on them until his back is bowing beautifully, and his come drips down Jacks hands, shuttering with his orgasm.

Quickly but gently, Jack takes off Bittys blindfold and, careful not to touch Bittys ass, scoops him up off the floor. Bittys arms loop around Jack immediately as Jack quickly moves him to the bed and rests him on his stomach.

"Was that okay, Mon amour?" Jack asks.

"Loved it." Bitty murmurs, sounding totally blissed out, then asks, "Did you come?"

"We can deal with that in a bit. First I want to get you cleaned up, yeah?”

Bitty hums happily and nods, relaxing against Jacks chest as he's lifted again and carried to the bathroom.

**Author's Note:**

> Yeah kinktober didnt work out so im gonna post random porn as I finish


End file.
